5-nitro-6-methylimidazo<2,1-b>thiazole | 62195-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并噻唑类
• 英文名称: 5-nitro-6-methylimidazo<2,1-b>thiazole
• 英文别名: 6-methyl-5-nitro-imidazo[2,1-b]thiazole；6-Methyl-5-nitroimidazo[2,1-b][1,3]thiazole
• CAS: 62195-26-0
• 化学式: C₆H₅N₃O₂S
• 分子量: 183.191
• InChiKey: UNLLIFOCJJPKKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-nitro-6-methylimidazo<2,1-b>thiazole 在 哌啶 、 sodium periodate 、 四氧化锇 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 54.0h， 生成 5-Nitroimidazo[2,1-b][1,3]thiazole-6-carbaldehyde
  参考文献：
  名称：

  Dihydropyridines bearing an imidazo[2,1-b]thiazole system

  摘要：

  This paper reports the synthesis of imidazo[2,1-b]thiazoles, bearing a dihydropyridine ring at the 5 or 6 position, which were tested for antiarrhythmic, inotropic and chronotropic activities. Nine of the ten compounds bearing double bond at the 2,3 position and the same dihydropyridine as nifedipine at the 5 position, were antiarrhythmic; moreover one of them (bearing a methyl group at the 2 position) was devoid of negative inotropic activity.

  DOI：

  10.1016/s0223-5234(97)87542-3
• 作为产物：
  描述：

  丙酮酸乙酯 、 5-nitro-6-chloromethylimidazo<2,1-b>thiazole 在 四(二甲氨基)乙烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以14%的产率得到2-羟基-2-甲基-3-(5-硝基咪唑并[2,1-b]噻唑-6-基)丙酸乙酯
  参考文献：
  名称：

  TDAE辅助合成新型咪唑并[2,1- b ]噻唑衍生物作为抗感染剂

  摘要：

  一系列新的咪唑并[2,1- b是在中度使用TDAE方法从6-氯甲基-5-硝基咪唑并[2,1-制备在四步合成法良好的产率]噻唑b ]噻唑和酮酯，ketomalonates和酮内酰胺。 测试了所有化合物对四种细菌菌株（两种革兰氏阳性和两种革兰氏阴性）和四种酵母菌的抗菌和抗真菌活性。在这些合成的5-硝基咪唑并[2,1- b ]噻唑类化合物中，化合物1和6对所有念珠菌菌株均显示出有效的抗菌活性，而化合物3e对热带念珠菌显示出有趣的抗真菌潜力。

  DOI：

  10.1016/j.ejmech.2009.10.048

文献信息

• Highly efficient microwave assisted α-trichlorination reaction of α-methylated nitrogen containing heterocycles
  作者：Pierre Verhaeghe、Pascal Rathelot、Armand Gellis、Sylvain Rault、Patrice Vanelle

  DOI：10.1016/j.tet.2006.05.081

  日期：2006.8

  A new methodology permitting the chlorination of different alpha-methylated nitrogen containing heterocycles into N-alpha-trichloromethylated derivatives is described here. The combination of microwave technology with a PCl5/POCl3 protocol has allowed to reach trichloromethyl derivatives with high yields in a few minutes. (c) 2006 Elsevier Ltd. All rights reserved.
• Winkelmann; Raether; Hartung, Arzneimittel-Forschung/Drug Research, 1977, vol. 27, # 1, p. 82 - 89
  作者：Winkelmann、Raether、Hartung、Wagner

  DOI：——

  日期：——
• Dihydropyridines bearing an imidazo[2,1-b]thiazole system
  作者：A Andreani、A Leoni、M Rambaldi、A Locatelli、R Bossa、I Galatulas、M Chiericozzi、M Bissoli

  DOI：10.1016/s0223-5234(97)87542-3

  日期：1997.1

  This paper reports the synthesis of imidazo[2,1-b]thiazoles, bearing a dihydropyridine ring at the 5 or 6 position, which were tested for antiarrhythmic, inotropic and chronotropic activities. Nine of the ten compounds bearing double bond at the 2,3 position and the same dihydropyridine as nifedipine at the 5 position, were antiarrhythmic; moreover one of them (bearing a methyl group at the 2 position) was devoid of negative inotropic activity.
• TDAE-assisted synthesis of new imidazo[2,1- b ]thiazole derivatives as anti-infectious agents
  作者：Thierry Juspin、Michèle Laget、Thierry Terme、Nadine Azas、Patrice Vanelle

  DOI：10.1016/j.ejmech.2009.10.048

  日期：2010.2

  A series of new imidazo[2,1-b]thiazoles was prepared in moderate to good yields in a four step synthesis using the TDAE methodology from 6-chloromethyl-5-nitroimidazo[2,1-b]thiazole and keto esters, ketomalonates and ketolactams. All compounds were tested for their antibacterial and antifungal activities against four bacterial strains (two Gram positive and two Gram negative ones) and four yeasts.

  一系列新的咪唑并[2,1- b是在中度使用TDAE方法从6-氯甲基-5-硝基咪唑并[2,1-制备在四步合成法良好的产率]噻唑b ]噻唑和酮酯，ketomalonates和酮内酰胺。 测试了所有化合物对四种细菌菌株（两种革兰氏阳性和两种革兰氏阴性）和四种酵母菌的抗菌和抗真菌活性。在这些合成的5-硝基咪唑并[2,1- b ]噻唑类化合物中，化合物1和6对所有念珠菌菌株均显示出有效的抗菌活性，而化合物3e对热带念珠菌显示出有趣的抗真菌潜力。